


Dressing Up

by TammyRenH



Series: Masquerade fills [3]
Category: Supernatural
Genre: Bottom Sam, Explicit Sexual Content, First Time Wincest, M/M, Possessive Dean Winchester, Sam In Panties, Sam in a Skirt, Semi-Public Sex
Language: English
Status: Completed
Published: 2020-04-15
Updated: 2020-04-15
Packaged: 2021-03-01 22:01:31
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,128
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23674291
Author URL: https://archiveofourown.org/users/TammyRenH/pseuds/TammyRenH
Summary: Fill for the following Masquerade prompt:  Sam can't really "pass" but the urge to get dolled up and go out to a bar to see what happens--see if some guy will take him home and take him apart--is too strong.When he finally tries it, Dean or John happen to be skulking around the same bar.During a summer break in Stanford, Sam gives in to the urge to get dressed up and go to a bar.  You’ll never guess who he finds there.
Relationships: Dean Winchester/Sam Winchester, Minor or Background Relationship(s), Sam Winchester/Original Male Character(s)
Series: Masquerade fills [3]
Series URL: https://archiveofourown.org/series/1701883
Comments: 12
Kudos: 157
Collections: SPN_Masquerade Spring 2020





	Dressing Up

**Author's Note:**

> My 3rd masquerade prompt and a really fun one to write! Who could resist Sam in a skirt and parties and Dean all possessive and growly?

For as long as he could remember, Sam had been a freak.  
  
First because of how his family lived, the hunting, the training, constantly being the new kid in an endless stream of schools.  
  
He would pray at night for a normal life, to wake up in a home (instead of a motel or a shitty rental or some run down cabin that belonged to a friend of a friend of a hunter Dad knew) and be just like any other kid.  
  
The morning he realized his prayers would never be answered, was the morning he awoke from his first wet dream. He had dreamt about Dean. It was a fairly innocent dream (especially contrasted with the dreams that came when he was older). Dean smiling at him, Dean leaning down, Dean’s lips just brushing against his –   
  
Sam had to make a mad dash to the shower. That was the first time he masturbated as well.  
  
As he got older, he discovered he liked boys just as much (and maybe even a smidgen more) than he liked girls. His first kiss was with a boy, Brandon, behind the gym on the day before he was to leave town. His first make out session was with Terrance, during the summer Dean was stocking groceries at the corner market and Sam was left alone for long periods of time. The first blow job (both giving and receiving), Simon of the long hair and the long fingernails that bit into his skin just right. The first time he had sex was actually a girl, Susie, a quick messy fuck on the couch, but it was soon followed by Gregory in the 18-year old’s grandparent’s pool house.  
  
It was actually Gregory that helped cement Sam’s freak status. Not with the sex, Sam was well aware that liking boys and girls both was perfectly normal and nothing to be ashamed of (although there was no way he would ever broach this subject with Dean – or heaven forbid – Dad) but because of the talent contest.  
  
Sam was on the basketball team. For years he hadn’t bothered with sports, because usually he had to move on before the season was over, but Gregory was on the basketball team and it gave Sam a reason to be late after school, an excuse to spend time with Gregory, so he joined. The starters on the team decided to enter the school talent show. When Sam protested he could neither sing nor dance, they laughed and said that was exactly the point.  
  
He had no real idea what they planned until they met for their one and only rehearsal the night before the talent show. “Here,” Gregory said, handing him a handful of clothes with a wink. “These are Tracy’s, she is the tallest cheerleader we have so hopefully these will fit.”  
  
“I’m fucking tall too dude.” Tim complained and Sam looked over to see Tim vainly trying to pull down on a very short, very bouncy cheerleader skirt. “I should have been given Tracy’s skirt. Fuck, if I bend over just a bit in this thing my junk is gonna fall out.”  
  
“Nobody wants to see that dude; your junk is probably as ugly as you are.” Gregory teased and turned back to Sam. “The bathroom is over there.” And as Sam walked by, he put his arm around Sam and whispered. “I bet you look really hot in that skirt.”  
  
The cheerleader outfit was red and white, the top was super tiny, and the skirt was really, really too damn short. Sam was torn between wanting to hide forever in the bathroom and wanting to see the look in Gregory’s eyes when he came out. Curiosity won, and Sam left the bathroom with his head down and his cheeks red. There were loud wolf whistles from the others, a few murmurs of damn son you really need to shave, but the way that Gregory looked him up and down, his pupils dark and blown wide, had Sam lifting his head high and feeling warm all over. Later that night, after their rehearsal of Mickey, complete with pom poms and played for laughs, Gregory fucked Sam against the wall in the locker room.

Sam left Gregory behind soon after that, but the look in Gregory’s eyes when he saw Sam in the cheerleading outfit stayed with him. He didn’t want to pass for a girl, didn’t think of himself as a girl. But every once in a while, when Dad and Dean were both safely hundreds of miles away on a hunting trip and Sam was home alone, he would pick up something soft and pretty to wear from Salvation Army or some thrift store. It never took long to find someone who would tell him how pretty he was, how great his ass looked in the too tight clothes, and then fuck him hard against any surface that happened to be available.  
  
And every time, every single time, it was Dean’s voice he heard in his head, Dean’s hands he imagined gripping his hips and holding on tight, Dean who he wished was taking him apart.  
  
College was a fresh start. In Stanford, Sam no longer had to be the freak. He gave up cross dressing, dated only girls, forced himself to stop thinking about Dean and could almost convince himself he was successful.  
  
But inside - there was an itch building. An itch that couldn’t be scratched by pretty little things flirting with him, offering themselves to him so sweetly. An itch that kept him up at nights, kept him on edge.  
  
He was sharing an apartment for the summer months with two other Stanford students, Sam worked at the bookstore to make ends meet until school started back and his scholarship kicked by in. His room mates were nice guys, studious, pre-law like him. They were fairly neat and very good about paying their share of the expenses, even if somehow it always turned out that Sam did most of the cooking (well if opening a few cans or reheating a pizza could be considered cooking) and cleaning up.   
  
It was nice to have them around. It was nicer when they both left during the 4th of July weekend to head home to be with their families.  
  
Sam went for a jog, made a few wrong turns, ended up downtown and in front of a secondhand clothing store.   
  
Thirty minutes later he had a purple skirt that didn’t quite make it to his knees, a dark pink shirt that didn’t quite make it to his belly button, and a park of flip flops with purple and black rhinestones.  
  
That night he shaved his legs, under his arms, his chest. He took hours to get ready, twirling around in the skirt since there was no one around to see him do it, adjusting the outfit just so. He put on the bubble gum lip gloss that he had kept hidden at the bottom of his duffle bag for years and could never bring himself to throw away. He fussed with his hair, finally pushing it back into a ponytail.   
  
He had grown a few more inches over the last year, and his body was still trying to catch up. He was too skinny, his hips too bony, his legs still looked coltish. Looking at himself in the mirror, he almost gave up - he didn’t look pretty, or enticing. He looked like someone playing dress up, he looked awkward and wrong and not even Gregory would find him pretty now.  
  
“Fuck it.” Sam said to the reflection on the mirror, grabbed his keys and headed out the door.  
  
He took a cab to the bar. He had scoped it out months earlier, a gay bar near midtown, a fairly upscale one at that, or so his research told him. He had never been in, had told himself he didn’t want to, that he had given all that up. But here he was, flashing his fake ID and stepping inside.  
  
The music was loud, something techno with a thumping bass line, Sam pushed past sweaty bodies and couples making out to sit on a stool by the bar. By then the music had switched to disco, and Sam sat on the stool, sipping on a whiskey sour, watching the crowd. Just when the alcohol had kicked in enough for him to brave the dance floor, he heard a whistle and spun to his side to see a man looking him over with unmistakable appreciation. “Fuck kid, those legs go on forever don’t they?” The man leaned in closer and whispered. “Can’t wait to see how fine your ass looks in that skirt.”

Sam’s mouth had gone dry. The man wasn’t a lot older than him, maybe about Dean’s age. He kinda reminded Sam of Dean with his pretty boy features, short spiked dark blonde hair. His eyes were a deep blue instead of green, which Sam told himself was a good thing. He definitely didn’t come here looking for a Dean substitute. And he certainly wasn’t so instantly hot and bothered because of the resemblance.  
  
The guy – Mike – bought Sam another drink before pulling Sam into the crowded dance floor. The music was so loud it was impossible to think, let alone talk. It wasn’t long until they were both sweaty and hard, their movements more grinding than dancing. Mike grabbed his ass and winked, and Sam was nearly delirious with desire for something other than dancing.  
  
It was clear Mike felt the same way, because before the song even ended, he had grabbed Sam’s hand and pulled him outside.   
  
It was a hot night, there were a few people milling around the parking lot. Sam made no protest when, instead of taking him to a car, he took Sam to the side of the building where they were partially hidden by shrubs that hadn’t been trimmed for a while and pushed him against the wall.  
  
“Look at you. So fucking pretty,” Mike’s hand grazed over Sam’s nipples and Sam arched into the sensation. He was covered in sweat, and the too small, too thin top was clinging to his body, his nipples clearly visible. “So hard for me already.” Mike said as his fingers brushed over Sam’s chest again. “Wonder what else is hard.”  
  
Sam never got a chance to respond, because Mike was yanked away. Eyes trying to focus in the darkness, and much slower to react than he should have been given all his training, Sam could see a shadow pushing Mike away, heard a familiar voice growl “Fuck off.”  
  
Sam was torn between his flight and fight response, as the struggle was over before it even started.“ Didn’t know he had a boyfriend. Maybe you should keep a better eye on him.” Mike snapped before walking away, not even looking in Sam’s direction before he disappeared around the corner.  
  
Sam started to move away from the wall, but he was slammed back against it and he was staring into a pair of angry green eyes. Impossible as it seemed, it was really him. It was Dean.  
  
Sam’s mind scrambled, trying to push through the panic and the alcohol haze. Dean was there. Right there. And Sam was – Sam was in a fucking skirt and oh shit, his nipples were practically visible through the thin material of his shirt.  
  
Sam started to fold his arms around his chest as he tried to come up with an explanation, but Dean grabbed his arms, pulled them back down. “No. You let him see, you damn well are going to stand there until I’ve looked my fill.”  
  
Sam shuddered and let his arms fall back by his side. His eyes were adjusting to the dark, he could see Dean as he stood in front of him, his hands clenched in fists, eyes travelled from Sam’s hair piled up in a ponytail all the way down, a leisurely stroll over Sam’s body.  
  
“Jesus, Sam.”   
  
“I can explain – “ Sam began, with no idea how he was going to finish that sentence.  
  
“I couldn’t care less about your explanations right now. You were letting that man touch you, take his greasy hands and run them across your chest. What was next? Were you going to let him kiss you? Fuck you? Were you going to get down on your knees for him Sammy?”

And really – fuck Dean. He had come out of nowhere, he was somewhere he shouldn’t even be. How many women had Dean taken to bed? How many one night stands? He was an alley cat; he had no right to pass judgement on Sam.  
  
“Fuck you!” Sam bit out. “I’m an adult, I can fuck anyone I want.“  
  
There was a low guttural sound emanating from Dean, that could only be described as a growl. Dean stepped closer, crowded Sam; Sam’s back was flat against the bar’s brick wall.  
  
“That goes both ways little brother, I can fuck anyone I want and tonight that is going to be you.”  
  
Sam was so shocked that he couldn’t grab onto a thought, or a feeling, and before he could open his mouth to say something – anything – Dean’s lips were on his, his tongue already pressed against his mouth, demanding entrance.  
  
And Sam was going to hell sure as certain, because he opened his mouth and he let Dean in. And in that moment Sam knew, whatever Dean asked for, he was going to give it to him and damn the consequences.  
  
There was something hungry about the kiss, something desperate and Sam grabbed onto Dean, clung to him like he was afraid he would float away if he didn’t.  
  
By the time they parted, they are both breathing heavily, and Sam could feel himself growing hard underneath the skirt.   
  
For a moment, Sam thought that Dean was coming to his senses and was going to bolt and his hands instinctively tightened around Dean’s neck, but he did neither of those things. His eyes searched Sam’s as if for looking for something and then he pushed Sam’s top up, until it is right below his armpits.  
  
They were very close together, so close that Sam could feel Dean’s belt buckle pushing against his skirt but somehow Dean managed to hold the top up with one hand, and the other reached for one of Sam’s nipples. Sam knew Dean was going slowly because he was waiting to see if Sam protested. Sam nodded his okay, pulled his bottom lip between his teeth.  
  
A finger brushed against a nipple and Sam’s body began to tingle. The finger flicked to the other one and Sam bit back a moan. Dean stepped back, forcing Sam to release his neck. “Off.” He ordered, pulling on the top. Sam didn’t hesitate, just pulled the top over his head and let it fall to the ground. He reached down hesitantly for his skirt, but Dean’s hands stopped him. For a moment Sam’s heart did a dive, thinking he misread Dean’s intentions, but Dean was smiling as he said “That stays on. Sexiest thing I’ve ever seen Sammy, you in this skirt. Those legs of yours, fuck.”

And then Dean knelt in front of him and if Sam had thought his head was spinning before, it was going full on Exorcist now. Dean’s hands stroked up and down his legs, stopping just short of the skirt hem before heading back down. “Fuck baby brother, you even shaved for this.” Dean’s hands reached higher, up into the skirt and Sam had to press his body back against the wall to keep from shaking. “Did you shave everywhere?” He asked, and then his hands stopped, and he looked up at Sam in surprise.  
  
Sam knew he had touched the silk and sure enough, Sam’s skirt was pushed up so that Dean could see what he had touched.  
  
Sam had found the panties in the secondhand store, still new in packaging and just had to have them They were pink, lace around the edges, soft and silky against his skin. They did nothing for his cock, which had already pushed itself free from its flimsy confines.   
  
“You are going to kill me.” Dean’s voice was actually shaking as his fingers caressed the bottom of the panties, caressed Sam’s skin there. His fingers bypassed Sam’s cock, followed the lace around his thigh and to his ass cheeks and Sam was already blushing, knew what he would find there. “Fucking hell Sammy, the panties are wet. Just like a girl’s would be.“  
  
Sam had planned to get fucked, so he had opened himself up before he left for the bar. He had used probably too much lube, because hell it had been a while. In the bar, while he was dancing, he could feel the lube escape the confines of his hole, slide through the panties, down the back of his thighs.  
  
Dean was pushing the panties down and a finger pressed in experimentally into his hole. It had been a few hours since he prepped, but he was still pretty open, could feel Dean’s finger slide inside with little resistance.  
  
Dean pulled his finger out. “Just asking for it aren’t you sweetheart? All wet and open for me. Turn around baby brother, let me give you what your greedy hole is begging for.”  
  
Normally dirty talk turned Sam the hell off but coming from Dean’s plush lips – Sam turned around so fast he made himself off balance, put his hands against the wall to steady himself, felt how his cock was leaking. He knew that his ass was now right in front of Dean’s face, and he could feel the blush form on his cheeks, and he was dizzy with want.  
  
Dean pulled the panties down past his ass, pulled the bottom of his skirt up. “You know why I love it when someone pretty wears a skirt?” He asked, as the finger reentered his hole. “Easy access.”  
  
Sam had never felt this unbearably turned on in his life, and the lack of shame he knew he should be feeling that it was his brother kneeling behind him, his brother pushing a finger in and out of him, just made him even more desperate.  
  
“Come on Dean, more.” He pleaded. “I can take it.”  
  
“So greedy.” Dean mumbled, and then stuck in another finger, all the way to his knuckle, without preamble and fuck it burned, and Sam still wanted more.  
  
He was faintly aware of being outside, of hearing muffled voices from the parking lot but he couldn’t bring himself to care. He was pretty sure they weren’t the first two to fuck against this wall.   
  
“Came out here, all dolled up, all wet and willing, just begging to get fucked.” Dean’s fingers were inside of Sam, twisting and scissoring and Sam’s head fell against the wall as he groaned. “Don’t you worry Sammy; I’m going to give you what you’ve been begging for. Hell, if I known you were this hot for it would have given it to you long ago.”  
  
Dean stood back up, hands circled around Sam’s chest, pressed against his nipples hard. “Last chance Sam, if this is not what you want, you’d better tell me now.”  
  
“Don't you dare stop.” Sam said in response and pushed his ass back into Dean’s groin.  
  
“Remember, you asked for this.” Dean responded and Sam could hear the sound of a belt being unbuckled, the zipper of Dean’s jeans being pulled down.  
  
One of Dean’s hands continued to roam his chest, fingernails lightly scratched his nipples which were hard and sore. The other guided Dean’s cock until it was pressed against Sam’s hole.  
  
Sam held his breath, too overwhelmed to make a sound. “You have no idea how long I’ve waited to do this.” The words were muttered against Sam’s back, tongue tasting the sweat that Sam knew had gathered there.   
  
And then Dean was pushing in, slowly, steadily. Sam arched against the intrusion, then let the air he had been holding in out, forced himself to relax. There was some discomfort, due to the length of time since he had prepped himself and how long it had been since he had been fucked, and Dean was big, not Sam-big but definitely there was more girth than Sam had taken before. Sam was so desperate for this, he would have endured much more pain than he was feeling to finally have Dean inside him.  
  
Dean stopped when he was all the way in, his head rested a moment on Sam’s back. Sam blinked back the tears from his eyes as he gave himself a few moments to adjust. Dean’s hands were now on his sides, roaming up and down soothingly, wordlessly asking Sam to tell him when he was ready.

Sam pushed back against Dean, letting him know it was okay and Dean pulled out and pushed himself all he way back in. He went slowly at first, carefully and Sam bit back a grunt of impatience, began to rock himself into Dean’s thrusts. He needed quick and hard and messy and Dean must have picked up on that because his grip tightened on Sam’s hips. “Hold on.” He warned before he began fucking into Sam in earnest.  
  
Sam’s body jolted with every thrust, but his arms kept him from being pushed into the wall. Sam’s body was tingling with how completely Dean’s cock filled him, he had never felt more alive, more present. Then Dean hit his prostate dead on and fuck, Sam felt a jolt of pleasure so intense that he must have let it escape with a shout. Dean gave a chuckle behind him, but his fast and brutal pace never wavered. “Shh Sam, we don’t want company for this. Or maybe you do. I’m getting the feeling you are one kinky son of a bitch.”  
  
Sam didn’t respond, couldn’t if he wanted to because he was being pounded so thoroughly his brain couldn’t catch on any words. Dean’s hand was on Sam’s back keeping it bent just so and he was hitting Sam’s bundle of nerves with every every other thrust, sending that jolt of pleasure so bright it was nearly pain. And fuck he was so hard. Sam started to take one hand from the wall but Dean bit into his back and then said. “I am going to get your there Sam, just be a good boy for me.”  
  
Time lost all meaning, Sam’s world was narrowed to Dean’s cock, fucking in and out of him, playing havoc with his prostate. His skirt was high up on his back, his panties were still mostly on except where Dean was pounding in, his cock was pressing against his skirt, tenting it. And fuck, he needed to come so bad. He reached for his cock again, but one of Dean’s hands left his hip, began to stroke Sam’s cock in time with his thrusts and Sam had to take the hand that left the wall and shove it into his mouth to muffle the noises that were coming out of him.

Dean’s thrusts were erratic now, slamming into him harder and his hand was hard and firm against Sam’s cock. The glide was too rough to feel good, yet somehow felt just right and Sam had just a moment to realize it was happening, before his balls tightened and his release came, spilling all over Dean’s hand and his panties, his skirt. His orgasm seemed to go on forever, his cock twitched as Sam’s body shook with the force.  
  
He tightened his ass when he came, deliberately, and was rewarded by a string of muttered curses before Dean’s release was filling him up, Dean was shuddering so hard he was shaking Sam and they both rocked through the aftershocks.  
  
For a long moment neither moved. It was the slamming of a door that penetrated Sam’s sex haze and apparently Dean’s too because he pulled out of Sam. Sam realized, as he felt come dripping down past his panties, that Dean had gone in bare but couldn’t bring himself to care much at the moment.  
  
The silence was deafening after what had just happened and Sam pushed his skirt down, picked his top up, turned around to face Dean who wouldn’t quite meet his eyes. A thousand questions skittered through Sam’s brain – why was Dean here? Had he been following him? What happens now? But it was Dean who spoke first, holding his hand out to Sam.   
  
“Come on, let’s get you home.”  
  
And Sam did what he had been doing since he could walk, he followed where Dean lead, followed him silently and willingly into the unknown.


End file.
